Cesium carbonate → HCID 68074158, compound

HRID 573735Notes

Reaction equation

HRID 573735 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11](I)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:33]1[CH2:38][CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH2:35][CH2:34]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+]>O.O1CCCC1.C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:12]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11]([C:36]3[CH2:37][CH2:38][O:33][CH2:34][CH:35]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 68061445HCID 68061445, compound

Product 1

HCID 68074158HCID 68074158, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Obtained by starting from (S)-ethyl 5-(tert-butyldimethylsilyloxy)-4-iodo-7,7-dimethyl-2-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydroquinoline-3-carboxylate and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. A 2 M solution of caesium carbonate in water is used instead caesium fluoride. The reaction is run in tetrahydrofurane/toluene 4:1.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-545ddea6258a4d30b86fb42439d909eb
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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